YHM - ORD

C$ 246 Find Cheap Flights from Hamilton to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hamilton to Chicago departing on 8/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hamilton to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hamilton to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 420
Multiple Airlines
Wed 8/4Wed 15/4
YHM - ORD • 1 stop
Cheapest one-way flights
C$ 246
Multiple Airlines
Wed 8/4
YHM - ORD • 1 stop
Direct flights
Not available
There are currently no direct flights between Hamilton and Chicago. You’ll need at least 1 connection.
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hamilton to Chicago (YHM-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hamilton to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hamilton to Chicago

Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:25 a.m. - 5:15 p.m.
YHM
-
ORD
10h 50m
1 stop
Multiple Airlines Logo
1:27 p.m. - 3:00 p.m.
ORD
-
YHM
24h 33m
1 stop
C$ 420Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:25 a.m. - 5:15 p.m.
YHM
-
ORD
10h 50m
1 stop
Multiple Airlines Logo
11:28 a.m. - 3:00 p.m.
ORD
-
YHM
26h 32m
2 stops
C$ 554Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:25 a.m. - 11:50 a.m.
YHM
-
ORD
29h 25m
2 stops
Multiple Airlines Logo
11:28 a.m. - 3:00 p.m.
ORD
-
YHM
26h 32m
2 stops
C$ 589Multiple Airlines
Sat, 25 Apr - Wed, 29 Apr
Multiple Airlines Logo
7:25 a.m. - 9:12 p.m.
YHM
-
ORD
14h 47m
2 stops
Multiple Airlines Logo
11:28 a.m. - 3:00 p.m.
ORD
-
YHM
26h 32m
2 stops
C$ 600Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:25 a.m. - 2:16 p.m.
YHM
-
ORD
31h 51m
3 stops
Multiple Airlines Logo
11:28 a.m. - 3:00 p.m.
ORD
-
YHM
26h 32m
2 stops
C$ 663Multiple Airlines
Wed, 8 Apr - Wed, 15 Apr
Multiple Airlines Logo
7:25 a.m. - 1:10 p.m.
YHM
-
ORD
30h 45m
3 stops
Multiple Airlines Logo
11:28 a.m. - 3:00 p.m.
ORD
-
YHM
26h 32m
2 stops
C$ 704Multiple Airlines
Mon, 27 Apr - Mon, 4 May
Multiple Airlines Logo
7:25 a.m. - 9:36 a.m.
YHM
-
ORD
27h 11m
1 stop
Multiple Airlines Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 749Multiple Airlines
Wed, 29 Apr - Wed, 6 May
Multiple Airlines Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
Multiple Airlines Logo
6:16 p.m. - 11:13 p.m.
ORD
-
YHM
51h 57m
2 stops
C$ 804Multiple Airlines
Thu, 21 May - Sun, 24 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:09 p.m.
ORD
-
YHM
27h 39m
2 stops
C$ 860Multiple Airlines
Fri, 29 May - Sun, 31 May
Multiple Airlines Logo
5:45 p.m. - 4:40 p.m.
YHM
-
ORD
23h 55m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:34 p.m.
ORD
-
YHM
28h 04m
2 stops
C$ 873Multiple Airlines
Booking Insights

Good to know

Cheapest flightC$ 246
Flight from Hamilton to Chicago

When to book flights from Hamilton to Chicago

Are your dates flexible? Find out the best times to travel from Hamilton to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hamilton to Chicago flights

  • What is the cheapest flight from Hamilton to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Hamilton to Chicago O'Hare Intl Airport was C$ 246 for a one-way ticket and C$ 420 for a round-trip.

  • Which airports will I be using when flying from Hamilton to Chicago?

    Hamilton airport is called Hamilton and the only airport in Chicago is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Hamilton to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Hamilton to Chicago?

    Star Alliance is the only airline alliance operating flights between Hamilton and Chicago.

  • How does KAYAK find such low prices on flights from Hamilton to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hamilton to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hamilton to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hamilton is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hamilton to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hamilton with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hamilton to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hamilton up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Hamilton to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Hamilton to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hamilton to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 10801 reviews
7.3Boarding
7.8Crew
6.3Food
7.1Comfort
6.8Entertainment
Airline reviews

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

2.0 MediocreFola, Feb 2026
YYZ - PHL
Read more Air Canada reviews

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff was great and made the long trip easy peasy!

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

Everything you need to know for your flight from Hamilton to Chicago

Information on your arrival and departure airports

Hamilton (YHM)
O'Hare Intl (ORD)